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While most episodes of Pokemon offer at least one or two battles with different trainers, the one event that always excites fans is the Pokemon League.
The Pokemon League is a tournament where the best trainers in the region compete for the title of champion. Since the beginning of the series, Ash has been a participant in nine tournaments of this kind, with some of them being more challenging than the others.
Here, we have attempted to rank all the tournaments that Ash has participated in, based on their level of difficulty.
Disclaimer: This list will be based on the author’s opinion and will contain spoilers from various Pokemon seasons.
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Orange Islands, Alola or Kalos: Which Pokemon League has been the most challenging for Ash?
9) Orange Islands
Orange Islands has always stirred controversy among fans. Since the season was created because of the delay of the new games Gold and Silver, a lot of fans take it to be non-canonical. But this was the first time that Ash won a league title.
Although Ash's last battle against Drake was long and tough, the rest of the league was far easier than others have been. The first two gym leaders in the region wanted to race against him, while the other two just had some quick and uneventful battles, making Orange Islands the easiest league Ash has ever had.
8) Unova
Even though Unova was not as easy as the Orange Islands, it was just as controversial. Ash’s team in the Unova region was not his best, but even then, it was not weak enough for him to have lost as badly as he did. His battle against Cameron lives in infamy because of the unfairness meted out to him.
After Ash had some uneventful battles in the league, he faced Cameron in the top eight. Cameron surprised most people when he started the match by commenting that he had only brought five Pokemon to the fight. Despite that, Ash could not win the league.
7) Hoenn
Ash’s Hoenn league was slightly more difficult than the previous ones, and while Ash did well during the league's two-on-two battles, he began to struggle when the six v six matches started.
He won his first two battles with just one remaining Pokemon, but his team went on to be defeated in pretty avoidable ways. His Pikachu was not as strong as it normally is, and was defeated by a Pokemon that should not have been able to do so: Ash fought valiantly against Tyson, but the latter's Mewoth proved stronger than Pikachu.
6) Indigo
Ash’s first league, and one of his best performances up until a certain point, he arrived here with a head full of dreams and a not-so-powerful team. Despite being an inexperienced trainer back then, he did quite well.
He was able to defeat many opponents with Pokemon that would not normally win, like Crabby, which had never been part of a battle. He went on to face Ritchie, who was just as inexperienced as Ash and had a bad team.
In the end, however, Ash's naievety and lack of training with Charizard led him to be defeated. Charizard refused to listen to him, resulting in his immediate disqualification.
5) Alola
Ash’s first win in a Pokemon League happened in Alola. Not only was this the first Alolan league ever in history, it was also one of the most unique ones in the series. To begin with, the preliminary round was not based on one-on-one matches, it was a battle royal from where only 16 trainers would continue.
This made things a little easier for Ash, since he was not going to have as many battles as he usually did, but that by no means indicates that he was not the strongest trainer.
He proved how ready he was by defeating Guzma and teaching him to be a better trainer. He also defeated Gladion’s Silvally, a Legendary Pokemon, in the semifinals. And his victory against Professor Kukui is still one of the best fights in the series. Overall, Ash's excellent performance made him truly deserving of winning this League.
4) Johto
The Johto league was a tough challenge for Ash, but brought out one of his best performances. After his previous losses, he decided not to rely on luck, and implemented what he had learnt from his past experiences.
This was the first time Ash was able to beat his rival Gary, using his most powerful Pokemon instead of his usual team. However, he was unable to win because Harrison had Pokemon from Hoenn, a region Ash had never heard of before.
This league is what motivated our protagonists to travel around the world, making it a memorable moment in the series.
3) Kalos
Ash’s team during the Kalos league was probably his best team yet, and he made that clear by taking on some of the strongest trainers in the series, with strategy and determination.
Ash defeated Sawyer by proving the strength of his passion, and was able to advance into the finals for the first time during this league.
In the last match, he faced Alain, one of the most powerful trainers in the entire world. And even though Ash fought with everything he had, he was still not able to beat the monster that is Alain's Charizard.
However, this league is still considered to be one of the best arcs in the franchise.
2) Sinnoh
The Sinnoh league is a controversial but beloved part of the series. Ash was ready to face anything that was thrown at him in this league, and refused to surrender. His first matches were a spectacle, and his strategies to win were top-notch.
When it was time to fight Paul, Ash was determined to defeat his most powerful rival yet. And even though Paul was presented as an unbeatable rival, Ash achieved the impossible by defeating him with Infernape, the Pokemon Paul abandoned.
The fight against Tobias, however, angered fans considerably. Not only did Tobias win the league by only using Darkrai, a legendary Pokemon, he also had Latios as a backup. While Ash was the only one able to defeat Darkrai, both Latios and Pikachu were rendered unable to battle at the same time.
Since Pikachu was Ash's last Pokemon, Tobias was declared the winner, but the league was proof of Ash's strength and capability as a trainer
1) Masters Championship
The Masters 8 championship is still ongoing, and represents a once-in-a-lifetime opportunity for Ash. Every champion is here, and they are ready to put their everything into the fight.
The members of the tournament include Ash, Iris, Alain, Diante, Lance, Steven, Cynthia, and Leon. The best trainers in the world, they are all determined to win the title of World Champion.
Ash's first battle will be against Steve, Hoehn’s champion, and judging by the sneak peeks, it promises to be a challenging one.
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